Acetic Acid → HCID 22282146, compound

HRID 1062579Notes

Reaction equation

HRID 1062579 reaction equation
[CH3:1][N:2]1[C:6]2=[N:7][C:8]([CH:13]=[CH2:14])=[C:9]([C:11]#[N:12])[CH:10]=[C:5]2[C:4]([CH3:15])=[N:3]1.C(O)(=O)C.[NH:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1>CO>[CH3:1][N:2]1[C:6]2=[N:7][C:8]([CH2:13][CH2:14][N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)=[C:9]([C:11]#[N:12])[CH:10]=[C:5]2[C:4]([CH3:15])=[N:3]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 31268PyrrolidineHCID 22282149HCID 22282149, compound

Product 1

HCID 22282146HCID 22282146, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1,3-dimethyl-6-vinyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile (2.20 g, 11.1 mmol) in methanol (110 mL) was treated with acetic acid (635 μL, 11.1 mmol) and pyrrolidine (4.59 mL, 55.5 mmol). The mixture was stirred at room temperature for 3 hours and the solvent removed under reduced pressure. The residue was suspended in water and extracted with ethyl acetate. The combined organic layers were dried over Na2SO4 and concentrated to give 1,3-dimethyl-6-[2-(pyrrolidin-1-yl)ethyl]-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile as a tan solid.

Workup

  1. customthe solvent removed under reduced pressure
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b2415eca13b34fa3b6dcbf906913d82f
Source dataset
uspto-grants-2005_11
Patent number
US06962926B2

Reaction notes

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